Sexcapades
by archard-winchester
Summary: A series of short one-shots of close calls Dean's had in his life. Almost all of them are cross-overs. Will update fast.
1. Chapter 1

A/N: This is a collection of cross-over fics. Mostly. Lets play "Guess the crossover". Click on review to play.

Disclaimer: I don't own anything. Doesn't mean I don't get to play with them.

Summary: Dean's life had a lot of close-calls. Some closer that the others.

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Looking into a case in a big city had its advantages. Hanging-out in a high-class night-club was not one of them. The place was a bit too clean, too quiet, too overpriced, too full of suits and too lacking in dumb patrons (hustling-wise) or hot chicks (single-type) for Dean's taste. Still there was a definite chance of his day getting better and that chance was walking towards him in a revealing green dress with piercing green eyes and a head full of luscious red hair.

"Are you him? Are you my mate whom I'm supposed to meet tonight here?"

OK. As punch-lines went that was way too direct. But he could roll with it. Hell, he'd dealt with his fair share of crazy chicks and left them happy and non-homicidal.

"Honey, it feels like I've been waiting for you my whole life. Where in the world have you been? No wait, that's not right. You are out of this world. You must be from some far off beautiful planet."

"It is you. I've been looking for you all over in this wasteland of a city. C'mon lets get out of here."

"Hey, what's the rush? Lets get to know each-other before. You know, what's you're your name and all that?"

"Whatever you say my love. I'm Maxi-."

"Dean. What are you doing?"

_I cannot kill him. He's my brother. I don't have anymore souls to sell._

"Sam. Little busy here. Can you come back later?"

Dean turned his attention back to the right place. Who was giving him a confused look.

"You are with this man? You are not alone?"

"Yeah. But don't worry about him. He was just leaving. Aren't you Sam?"

"You are not him."

Giving Dean a last disappointed look, the girl turned around and started walking away. Girls didn't just walk away from Dean Winchester. That just wasn't right. Sudden comprehension dawned on Dean.

"No, no, no, no, no. He's my brother. My soon to be absent brother. He's not with me. Not like that. Really, I'm straight. We're not together. Dammit Sam."

Sam was somewhere between exasperated and amused.

"What the hell Sam? That chick was totally coming on to me. I was so close that this whole thing was practically the morning after. And you blew the whole thing for me.

"Dean, I don't think it's the best idea to hook up with random girls in a city where men are dieing due to sex hormone overdose. C'mon we need to get back to the case. Lets go."

Dean took a last wistful look at the object of his temporary affections who had found her own new object of affection.

"Man, she's with some bow-tie photographer geek now. I'm counting this one as a score."

"You keep score Dean? That's kinda sad."

"Shut up. You ruined my night. No more driving privileges till you find me a new one. Lets get back to the man-killing sex-machine case."

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	2. Chapter 2

A/N: This is a collection of cross-over fics. Mostly. Lets play "Guess the crossover". Click on review to play.

Disclaimer: I don't own anything. Doesn't mean I don't get to play with them.

Summary: Dean's life had a lot of close-calls. Some closer that the others.

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Sam looked-up from the laptop and searched the crowded bar for his brother. There he was, with…. a blonde. As expected. He sure knew how to pick them. Even if this one wasn't a total knock-out she was pretty hot. In fact, Sam realized after looking around, she was the best option there. Sam gave the girl a once-over. Even if he didn't hit on anything with legs, he could still appreciate beauty. And this one was pretty appreciable. And with good legs. And long blonde hair, almond-shaped eyes, cute upturned nose, long slender neck and ….. wait a minute. Sam looked confusedly at the girl again and started walking towards what he realized to be his very buzzed brother.

"Hey Dean, my man. How's it hanging?"

Dean's look said to him- Go away Sam.

"Dean? I thought your name was Conrad."

"Dean's a nickname." 'Conrad' explained.

"Oh, I'm so sorry 'Conrad'," with air-quotes if someone missed the inflection, " I didn't realize you came back for another round. I thought that after the one in the bathroom…"

Dean's look said to him- What the hell Sam?

"Hey, since you and Cindy have an open relationship and all, you think she'll give me chance?"

Dean's look said to him- I'm gonna kill you Sam.

Dean's date looked at him weirdly and said, "I think should go. I never realized it was so late."

Dean fumed for two whole minutes before he could get any words out.

"Sam, what the hell were you doing? If you think this is funny, I'm gonna…."

"Relax, Dean. I was doing you a favor."

"A favor? By saving me from getting laid."

"By saving you from an embarrassing situation. If you had looked a little above her breasts, you would have noticed she had an Adam's apple."

"What are you talking about? Girls don't have Adam's apples. That's just… oh my God."

"Exactly."

"Y-you mean…. She was a ….. he?"

"Yup."

"Dammit. I should have realized it sooner. I mean , who names their kid Carmalita?"

"You didn't realize there was something weird with a name like that. That was just too exotic to be true Dean. Its the name of some kind of Politician's mistress."

"Oh man. That was a close one. Sam. I take it all back. You are the best brother a guy could ask for. Even if you could have handled it better."

"You're welcome. You gonna get back to hook-ups."

"Nah. Lets go back to the motel. That was too close a call for a second round."

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	3. Chapter 3

A/N: This is a collection of cross-over fics. Mostly. Lets play "Guess the crossover". Click on review to play. For this one, F-bombs ahoy.

Disclaimer: I don't own anything. Doesn't mean I don't get to play with them.

Summary: Dean's life had a lot of close-calls. Some closer that the others.

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The girl was drunk. Though technically, she was a woman. And quite older than Dean. Which was not a problem with him because he liked older women. They had experience, stamina and by looks of this one, flexibility. Besides, she was very hot. Kind of in a hot-soccer-mom way. And way too drunk to have any inhibitions.

"My first husband was an asshole." She slurred

"Really. What about the second one?" Just being polite.

"He was an asshole too. But I wanna talk to you about the first one. Its like I didn't even know the guy. Its like he had this whole fucking life without me which I had no idea about. I still have no idea about. That bastard had other kids and he never told me."

"What a jerk. Cheating on a great girl like you."

"Oh, he didn't cheat on me. He had kids from his first marriage. Which he told me nothing about either. He was a traveling salesman. He'd be with us for a week out of a month at the most. And rest of the time he'd spend going around the country with his fucking kids. But you know what, I don't wanna talk about it."

"Sure. So how about we get out of-"

"You know who's an even bigger asshole."

*Sigh* "Who?"

"Andy. My brother-fucking-in-law. That lying ass didn't even tell me about all this till I forced it out of him. He didn't tell me that Judah had changed his name when his parents got divorced. He didn't tell me that he disappeared for a lot of years after his wife's death before resurfacing and getting his old name back. And he never told me that that asshole had kids stashed away somewhere with whom he spent three-fourth of his fucking miserable life. If my jack-ass of a father-in-law hadn't let it slip, I would never have found out. This will fuck my kids up for good. As if they weren't before."

"That's tough."

"Oh no, that's not the worst. That asshole died on some god-forsaken, back-country shithole hospital. And his kids just took him away. And that bastard Andy. He told us that the hospital had already cremated him. You see? My kids don't even get to say good-bye to their dad. All they get is a tomb-fucking-stone."

"That's harsh." Get over it lady. We've all got problems.

"You know, when we started talking, I decided I was gonna screw you."

Finally. "Really? Looks like we've got something in common."

"But I'm not gonna anymore."

Damn. Don't tell me all that suffering was for nothing.

"Why not?"

"Nothing against you. Its just that you remind me of 'him' a bit. Besides my current boyfriend is a drug-lord and a mafia boss. I'd be doing you a favor by not fucking you."

"A drug-lord huh? So what do you do for a living?"

"I sell drugs too. I'm a weed dealer. That's how we met."

Okay. Either this chick was bat-shit crazy or too screwed up. Either way he had a great out.

"Hey, too bad. Can't win them all. Can I atleast have your name?"

"Nancy."

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	4. Chapter 4

A/N: This is a collection of cross-over fics. Mostly. Lets play "Guess the crossover". Click on review to play. For this one, F-bombs ahoy.

Disclaimer: I don't own anything. Doesn't mean I don't get to play with them.

Summary: Dean's life had a lot of close-calls. Some closer that the others.

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Dean rolled on his back, off a sweaty, panting girl tangling them both in sheets. Miami was hot to begin with and high energy sex made it even hotter.

"Wow" The girl let out. Something every guy wants to hear in the end.

"I know."

"I mean, WOW. You were fucking amazing, Max. You fucking blew my mind away."

"I know. And that was some of my best work too."

"Geez, modest much."

"Hey, you know you were great too. I finished, didn't I?"

"You humility is unbelievable."

She let out a contented sigh and snuggled closer to Dean, letting her eyes droop to sleep. But Dean, not being sleepy, didn't let that happen.

"So, Deborah, nice place you've got."

"Seriously? That's your idea of post-coital talk?"

"Hey, we just met. Throw me a bone here."

"Last I remember, you were the one throwing bones. Anyway, this place is not mine. Its my brother's. I'm just crashing here for some time."

"Bother huh? Overprotective, shoot-you-with-a-shotgun-if-you-look-at-my-sister kinda brother?"

"No, you-slept-with-my-sister-so-lets-be-best-friends kinda brother. Besides he's spending night over at his girlfriend's tiday. Now would you let me sleep? I've got an early day tomorrow."

"Really? What do you do?"

"I'm a cop. And I have to go after a serial killer tomorrow morning."

"Yeah, been hearing about that one. So you are one of the butcher cops? You guys any closer to nabbing that guy."

"I can't talk about that. Besides this is a new case coming in tomorrow. Some suit called Hendrickson got a tip-off about his guy being in Miami. Dean Worcester or something. This dude breaks one traffic signal and has his photo raising all kinds of alarms in the database."

"Wow, that's pretty high tech. You guys do that kinda thing for all criminals of just serial killers."

"I dunno. Hendrickson must've flagged him or something. Now let me sleep or I'll blow you balls off."

Two seconds later.

"So what does your brother do?"

"He's in the department with me. Now would you let me sleep."

"I don't know. I'm getting kinda hungry."

"Then go make yourself a sandwich or something. Don't disturb me."

Dean got up putting on his boxers and jeans. This was going to be tricky. He had to leave without making it seem like he was nervous. And raising her suspicions. First order of the day was to turn off her cell. So that if Hendrickson made it here earlier and went around messaging his photo to cops, there's atleast be one less cop on his ass. Next, message Sammy. "Get 2 secure location. Call me after." Next, check out the info they had on him. A reply message from his brother told him his instructions were being followed. Dean went ahead to the living room where he'd seen a computer. One that was most likely used by the cop siblings to do case research.

Access password protected. Too easy. He didn't go around hacking PC's like his brother but he knew more than enough about it. Enough to get into the Miami Police Department's database's recent pages within five minutes. And that's where he hit paydirt. The most recent page had his file, his rap-sheet and MO. Other pages involved the addresses of different cemeteries in Miami, with those in secluded areas far away from main city paid special attention. Made sense. A guy who liked to dig-up graves for kicks would go for a secluded far-off area at night. The only reason the whole department wasn't notified was probably because this guy was trying to be a hero and nab the notorious Dean Winchester all by himself. Dean checked which cemetery addresses were visited more than twice to find out which one would be his priority. Yup, he picked one of the more secluded ones that was near the city limits. Also near a constellation of motels. This guy was good. But luckily for the Winchesters, neither the cemetery on their list nor their motel one of that group. They were safe for now. As if on cue, his cell buzzed.

"Hello."

"Dean. What the hell's going on? Are you alright? Where are you?"

"One question at a time Sammy. I'm safe. I'm with a cop, who accidentally tipped me off that Hendrickson's coming to town tomorrow. Today, infact."

"Son of a bitch."

"Yeah. We'll have to bail on this case. How did the interview with the widow go?"

"Don't worry about the case Dean. She'd seen her husband quite a few times, so it was pretty easy to convince her about the ghost. But she'd cremated her husband."

"So, no bones?"

"No bones. But the spirit was attached to his pocket-watch. I burned it."

"You sure?"

"Yeah, I'm sure Dean. The EMF went nuts near it. Anyway, the widow's burning rest of her husband's belongings. Just to be sure."

"Thank God. Anyway, where are you now?"

"I'm back at the motel. Don't worry, the perimeter's secure and no one followed me here. I'm monitoring the police radio for good measure, but not a blip on us yet."

"Good. Start packing. I'll be back soon and then we'll blow this joint."

"Dean, this will have to be a fast drive. We're near the coast, so the directions we can go into are pretty limited. I think it would be easier if we-."

"No Sam. We are NOT leaving my car behind."

"I'm just saying. She'd safe. We could change her- its-."

"Her."

"-her license plates. And then Bobby could-."

"No way Sam. You don't leave family behind."

"Alright, geez. Just a suggestion."

"Yeah, a stupid one. I'll be back in a jiffy, so start packing. Bye."

"Bye."

Dean shut-off the phone and then shut-off the computer, not bothering to cover the tracks of his recent break-in. Deb was going to go crazy when she saw his face on the board anyway. He went back to the room and started putting on his shirt with a half-asleep Deb waking up.

"Hey, heard you talking. Is Dexter back?"

"Your brother? No. I was talking to my brother. He's in bit of a jam. You mind if I go and bail his ass out."

"Sure. So, will I see you again?"

"Definitely. I'll take you out tomorrow night. Can I have your number?"

Because a beautiful girl's number was a terrible thing to waste.

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	5. Chapter 5

A/N: This is a collection of cross-over fics. Mostly. Lets play "Guess the crossover". Click on review to play.

Disclaimer: I don't own anything. Doesn't mean I don't get to play with them.

Summary: Dean's life had a lot of close-calls. Some closer that the others.

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They said that there were five stages of death. Denial, anger, bargaining, depression and acceptance. But Dean knew that where death by fratricide was concerned, there were only three. First, Sam's face getting screwed up, his eyes going narrow and the whole thing freezing up. Second, Sam taking deep, calming (useless) breaths like a woman in a pre-natal class. Third, the vein in Sam's forehead popping apoplectically. Well, four if you considered a bullet between the eyes as a step. Dean didn't think he'd ever seen the face so screwed-up, the breaths this deep and the vein so violent before. He looked around the room surreptitiously, simultaneously trying to get a clue about his crime and making sure there was no gun within Sam's reach.

"You stupid, selfish, horny son-of-a-bitch."

"Sam, whatever it is that's got you so worked up, I can explain."

"Yeah?"

"Yeah. Its not my fault."

Two deep breaths. Then another two.

"Dean, Bobby called. There is a detective looking around for you. Bobby headed him off."

"And?"

"And, the detective was hired by your wife to find you."

"What? That's not possible. I'm not married."

"Yes you are. I checked the marriage records. One Dean Winchester of Lawrence Kansas is married to…."

"Oh no." Dean slapped his forehead in as his memory returned. "Dude, I totally forgot."

"That's what you are going with? You forgot? Dean, of all the brainless, idiotic.."

"Sam, cut it out. This one does not count. Whatever happens in Vegas stays in Vegas."

"It did not happen in Vegas Dean, it happened in Washington DC. And whatever happens there goes all around the world."

"That can't be right. I never once got married in Washington."

"Never once.. Dean, how many times have you been married?"

"Just once, I swear. I have only one wife, my darling Astrid."

"Her name's Angela."

"That's what I meant- Angela Briggs."

"Angela Montenegro."

"Right, that's the one. I got married to her on Fiji Islands. Man that was wild."

"How did you get to Fiji?"

"It was a whole haunted cruise ship case. Way back when you were at college. I met this crazy hot chick, who was totally into me. Only she'd promised her dying mom that she'd save herself for her husband, or something like that. Total bullshit, man. She was not saving anything for anyone. So we just got this idea to get married for one night and in the morning I almost missed my liner, so I had to go and then I just, kinda forgot."

"You forgot? You FORGOT?"

"Sam, calm down. You'll burst a vein. Besides, why is she looking for me? Can't she just claim divorce by abandonment or something?"

"Actually, it seems that you both abandoned each-other. So unless they know who abandoned who first, they can't get you divorce."

"That's just nuts. Wait a sec, shouldn't she be off the hook ever since I've been declared dead and all."

"Which time?"

"The first time."

"No Dean, you are not officially dead. The FBI released a press statement of you death but they are still looking for us. They just want us to let our guard down. They suspect that we were responsible for exploding police station."

"Yeah, I know that. But this girl shouldn't know that right?"

"Well guess what? She works for the FBI. Not an agent but some sort of forensic specialist."

"Great. That's just peachy. We can't go up to her and ask her for a divorce now."

"No we can't, can we?"

"Stop being snide, Sam. This is a serious problem. I'm married to an FBI chick."

"I know. Another thing you'll have to pay for when they catch you. Alimony."

"Laugh it up, smartass. I've too get it annulled somehow without blowing my cover. Otherwise… hey Sam, what will happen if I don't get this annulled."

"Well, you won't be able to marry again, you idiot."

At that, Dean's face fell. He thought it over in a depressed tone.

"I won't be able to marry. You mean, if the love of my life comes along, a girl with whom I wanna spend the rest of my life with comes by, I won't be able to marry her."

Sam's heart went out for his brother. Dammit, Dean just couldn't catch a break could he? He felt his anger drain away as the need to comfort his brother took priority.

"Dean, it'll be fine ok? We'll find a way. Give them your death certificate or something. That way you should get your divorce."

"No way. I'm not getting a divorce."

"What?"

"Don't you see Sam? I've got the perfect excuse never to marry. Because I'm already married. Can't get a divorce, because that'd land me in jail. I'm the perfect bachelor. I'm every straight guy's dream come true."

"But- but what about the right girl thing?"

"You think the love of my life would care if I'm married to her or not? No Sam. This is perfect. This is better that perfect. Its just too good. This is the best thing that's ever happened to me."

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	6. Chapter 6

A/N: This is a collection of cross-over fics. Mostly. Lets play "Guess the crossover". Click on review to play. This one is set in Ist season.

Disclaimer: I don't own anything. Doesn't mean I don't get to play with them.

Summary: Dean's life had a lot of close-calls. Some closer that the others.

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In their field of work contacts meant everything. Keeping up-to-date with the lives of all the people they'd met was important. Which was why Sam was spending his downtime, checking the voicemail messages on their old numbers. His, Dean's and Dad's. Which was getting a tedious since they'd not been checked for a few months and Dean was apparently a man-whore.

"Message No. 23" the monotone went.

"Hey Dean. This is Carly. I was wondering if you were coming by the town again. I got some new stuff I wanna try out and –"

Click. "Message erased. Message No. 22"

"Hi, uh Dean. Its Julie. Uh.. so we never got to do the second da.."

Click. "Message erased. Message No. 23" Sam wasn't sure if he could take much more of this.

"Dean, hi, umm, this is Erica from Ohio." There it goes. Again. " Umm, I didn't wanna tell you like this but I'm, uhh, pregnant. So I was thinking maybe we should talk. You know about the baby and everything. Ok, so call me. Whenever you get this. Oh and by the way I baby's yours. I think atleast. Bye."

Well that was new.

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"So, Erica called." Sam informed Dean as the elder Winchester came back with the food supplies.

"Who?"

"Erica. From Ohio."

"Ohh.. Who?"

"Dean, how many Ericas from Ohio do you know? Wait, let me rephrase that. How many Ericas from Ohio have you slept with?"

"Do I look like the guy who keeps score? C'mon Sam, you know me better than that."

Seeing his brother's outrage, Dean felt obliged to explain.

"Dude, it's a whole state alright."

"Well, let me narrow it down for you. It was a little more than a year ago and Dad had sent you on that job alone. Ring any bells?"

"It'll come to me. What's with the clues. Spill it out already. So she called you in the morning and…?"

"No, she called you, six months back, on your last number. To tell you that she was pregnant."

The statement had every bit of the dramatic effect that Sam had hoped for. The shell-shocked look and then the weak laugh.

"Ha ha ha. Very funny Sam."

"Dean, I know this is your worst nightmare, but I'm not kidding. Here, listen to the message yourself."

Sam tried not to laugh as he watched his brother listen to the message. He really did.

"Not funny Sam. This can't be true. This has got be some sort of con. She is trying to get me to pay child-support."

"Because you are so obviously rolling in money."

"Then she's trying to get me to call her back. She just can't get enough of me."

"She's not doing anything of the sort. Dean, really, the rate at which you go around with the girls, this had to happen sooner or later."

"Why the hell not later, dammit? I'm too young to have kids. Seriously, how dumb do you have to be to get knocked-up by a stranger in this day and age?"

"You are the one who knocked her up."

"Still… wait a second. Erica? Yeah, now I remember her." A sudden look of relief washed over Dean. "Phew. Had me going there for a moment Sammy."

"Wait, so you remember her now?"

"Yeah. Met up with her in a bar. Not the brightest bulb, you know, but kinky as hell. Spent a crazy night with her and fed her some crazy story about being on run from the cops because I took a shovel to my dad's head. And she believed it. Yup. No way did I knock her up."

"How? How are you so sure? Because I gotta tell you Dean, even if you were safe, those things are only about 97% effective."

"Nah. She just couldn't have gotten pregnant the way we had sex."

"So, you mean, instead of going upfront, you…"

"Totally. Told ya. Kinky as hell."

"You're disgusting."

"I know."

"And that girl's really dumb not to have realized this still."

"I.. you called her?"

"Yeah, I had to find out about my nephews or nieces."

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Later in the car.

"So, what did she do with the baby?"

"Why do you wanna know?"

"Sam, this could've been my kid. Almost was. I guess this makes me the godfather or something."

"No it doesn't. Anyway, she had twins. A boy and a girl. And she gave them up for adoption."

"That's nice. She tell you who did she give them to?"

"Yeah. A couple in New-York. Monica and Chan-something Bing."

"What? No way Sam. We gotta get those kids back."

"Why? You know them?"

"No, but a name like Bing? No way that can be healthy for a kid. I mean that borders on child abuse. So what do these Bings do?"

"Erica wasn't sure. She first thought that "she" was a reverend and "he" a surgeon. Now she's sure that "she" is a chef."

"And what about him?"

"No-one seems to know the answer to that."

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Press the button. You know you know it.


	7. Chapter 7

A/N: This one's not a crossover.

Disclaimer: I don't own anything. Doesn't mean I don't get to play with them.

Summary: Dean's life had a lot of close-calls. Some closer that the others.

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Stupid Dean. And his stupid games. Seriously, who plays 'I Never' with his own brother. A guy who you know completely already. Stupid people, that's who. Sam looked up and saw Dean smirking. Both of him. Stupid tequila.

"So Sammy, my turn." How much can that guy put away." I never… had a threesome."

Stupid Jess. And her stupid friend. And her stupid fantasies.

Sam gulped down the shot and barely kept it down.

"Way to go Sammy. You are so telling me all about it. When I'm sober." Dean cheered.

"What are you so happy about?" Sam sulked." Hey, you gotta take a shot too. You've had a threesome before. "

"Yes you have. The twins, remember. I saw you."

"Ohh, yeah. Forgot about that. Anyway that doesn't count. They were twins. They were practically the same person."

"It does count."

"Alright then." Dean took the shot. "Your turn Sam."

"Last one alright."

"Ok. After this, its free for all."

"I never.. had a girlfriend of the dead variety."

Dean paused. Then took the shot. And Sam sobered up.

"Dean. What the hell?"

"Calm down Sammy. She wasn't my girlfriend per-se."

"Then?"

"She was kind of… my wife."

"Dean. What the hell were you thinking? What was she? A zombie? A vampire?"

"A ghost."

"You married a ghost? What you couldn't tell she was alive?"

"Get your panties out of the bunch Sam. It was just a job alright. The chick got killed on her way to church on her wedding day. And she wouldn't move on till she got married. And she was cremated. So I just gave her what she wanted."

"So you didn't sign any license."

"Nah. She just wanted a priest and some guy to say 'I do'."

"Dean, you are crazy."

"Hey, don't blame me. It was Dad's idea."

"Well, then my whole family's crazy."

The brothers sat in silence for a moment, with Dean filling up another shot.

"Hey Dean suppose if just marriage hadn't been enough for her?"

"What do you mean?" Dean said bringing up the shot.

"Suppose she wanted to be, not a bride but a wife."

Whatever reaction Sam had been expecting, it was not getting sprayed with tequila as his brother went into a coughing fit.

"What the hell Sam?"

"What's wrong with you Dean?"

"Don't scare me like that again."

"You spat all over me, you jerk."

"Well then don't say things like that again… bitch."

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